Eventually I would like to build a duplex and house hack with STR in the area.  

I've done some research and have a strategy, but I want to do this in the most legally sound and tax-efficient way possible while avoiding unforeseen pitfalls.My Goal:To consolidate my two current rental properties into a property that will initially serve as a rental and eventually become my primary residence in retirement.My Plan:Here is the step-by-step strategy I've put together: Sell my two rental properties (VA Loans) and execute a 1031 exchange, rolling the proceeds from both sales into the purchase of a single investment property.

It adds up fast.On estimating other expenses for the Philly metro area, here are some ballpark numbers per unit per month that I use as starting points:- Water/sewer: $50-80 (if landlord-paid, which is common in older Philly multifamily)- Insurance: $80-120 per unit (get actual quotes — this varies a lot by neighborhood)- Property taxes: Pull from county assessor records — Lehigh County and Philadelphia have very different rates- Vacancy: 5-8% in those markets right now- Property management: 8-10% if you plan to outsource eventually (budget for it even if you self-manage — your time has value)One tip that saved me a lot of headaches early on: before you make offers, build a simple deal analysis template where you plug in purchase price, rent, and all these expense percentages.

When you eventually sell, the IRS recaptures depreciation at 25% on the accelerated portion.

Much of my current work is foundational: land stewardship, small-scale provision projects, and community-oriented initiatives that will eventually integrate with housing stability and local investment.

To answer your questions, we apply late fees consistently every month and they eventually do pay the entire payment in that month.

Thank youHi Lynn, it might not be totally impossible but the tricky part in your situation is the Medicaid piece, because when someone is on Medicaid and moves permanently into a nursing home the state can eventually try to recover costs from their assets through something called Medicaid estate recovery, which means the family often just wants to sell the property quickly and cleanly rather than do creative terms like seller financing or long payment plans.

Eventually I'd like to refinance and pull out cash to move into my next deal.

If they’re helping with tax strategy, planning, and bigger-picture decisions, that’s where advice can be worth it.One other thing many investors eventually learn is that traditional brokerage accounts are just one bucket of capital.

Eventually, I resigned my commission, walked away from grad school and active duty after 13 years, and went full-time in real estate.Since then, I’ve worn a few hats:FlipperReal estate agentRental owner/operatorOff-market acquisitionsSmall land development and infillToday I’m in Boise doing high volume.